Fresh Air - Best Of: AI's Writing Critique / The Rise And Fall Of Condé Nast

Episode Date: August 15, 2025

After writing chapters of her new book about how tech companies help and exploit us, tech journalist and novelist Vauhini Vara fed those chapters to ChatGPT. She told the AI chatbot she needed help with her writing. But her real goal was to analyze and critique the chatbot’s advice. Her book is Searches.  Also, before social media, before influencers, the magazines Vanity Fair, Vogue, GQ, and Architectural Digest were among the most significant tastemakers, informing readers what clothes, celebrities, and trends were hot. We’ll talk with Michael Grynbaum about how Condé Nast cultivated a mystique that captivated subscribers. Learn more about sponsor message choices: podcastchoices.com/adchoicesNPR Privacy Policy

Support for NPR and the following message come from the Walton Family Foundation, working to create access to opportunity for people and communities by tackling tough social and environmental problems. More information is at waltinfamilyfoundation.org. From W.HY.Y and Philadelphia, this is Fresh Air Weekend. I'm Sam Brigger. Today, tech journalist and novelist Wahini Vara. After writing chapters of her new book about how tech companies both help and exploit us. She fed those chapters to chat GPT. She told the AI chatbot she needed help with her writing, but her real goal was to analyze and critique the chatbot's advice. Is it ethical to

mislead a chatbot? A hundred percent. I say that as a journalist, with the full expertise and authority of my role as a journalist. I think our relationship with these products is really different from our relationships with other human beings. Also, before social media, before influencers, the magazine's Vanity Fair, Vogue, GQ, and Architectural Digest were among the most significant taste makers, informing readers what clothes, celebrities, and trends were hot. We'll talk with Michael Grinbaum about how Condé Nast cultivated a mystique that captivated subscribers. That's coming up on Fresh Air Weekend. There is so much happening in politics in any given week. You might need help putting it all

perspective. As your week draws to a close, join the NPR Politics Podcast team for our weekly roundup. Here, our best political reporters zoom into the biggest stories of the week, not just what they mean, but what they mean for you, all in under 30 minutes. Listen to the weekly roundup every Friday on the NPR Politics podcast. Support for NPR and the following message come from the Walton Family Foundation, working to create access to opportunity for people and communities by tackling tough social and environmental problems. More information is at walton family foundation.org. This is Fresh Air Weekend. I'm Sam Brigger. Terry has today's first interview. Here she is. Here's the kind of conflicted relationship my guest has with big tech.

Tech journalist and award-winning novelist Wahini Vara has ethical reasons why she shouldn't shop on Amazon and at least as many reasons why she does. Then there's Google. She's opposed to how Google monetizes our personal information to sell ads geared to our interests, but she appreciates the archive of her own stored searches, many of which she lists in her book because of what they reveal about different periods of her life. As a tech reporter, she got access to a predecessor of ChatGBT. She loves playing with AI, and has found ways it can be helpful. But she's skeptical of its use as an aid for writers. She's written twice about testing. a chatbot in that capacity, first in an essay that went viral called ghosts, in which she asked

AI to help her write about her sister's death. And now again, in Vara's new book, Searches, Selfhood in the Digital Age. After she wrote chapters of the book, she fed the chapters to chat GPT and asked for help with her writing. Then she analyzed the advice and what it says about the abilities, shortcomings, and biases of the chatbot. She asked, her interactions with ChatGPT to her book. The theme of the book is how tech is helping and exploiting us. Vara started as a reporter at the Stanford University campus paper, where she edited its first article about Facebook when Stanford became the third university to get access to it. She covered tech for the Wall Street Journal, was a tech writer and editor for the business section of the New Yorker's

website, and now contributes to Bloomberg Business Week. Her novel, The Ombudsman, Mortal King Rao was nominated for a Pulitzer Prize. Her short story, I Buffalo, won an O'Henry Award. Well, Haini Varo, welcome to Fresh Air, and thank you for getting here. Your windshield got shattered by who knows what. On the way over to the studio, I'm so grateful to you for making it. It was worth it. I was like, I'm getting to that studio. And you did. Thank you. And welcome, and I enjoyed your book. So you did this exercise of feeding chapters of your book to chat GBT asking for advice. What did you tell the chatbot? Why did you tell it you wanted its help? I'm glad you asked the question that way because I'm really interested in the way

in which we sort of perform different versions of ourselves when we communicate, whether it's with other human beings or with technologies. And so I was definitely playing a role with the chatbot. I told the chatbot that I needed help with my writing. And I was going to feed the did a couple of chapters of what I was working on and I wanted to hear its thoughts. The reality was that I wanted to see how chat GBT would respond. And so the interplay between sort of my performance and its performance was super interesting to me. I have an ethical question for you, Wahini. Is it ethical to mislead a chat box and ask questions under a kind of false pretense? A hundred percent. I say that as a journalist with the full expertise and authority of my role as a journalist. You know, I think so. I think our relationship with these products is really different from our relationships with other human beings. I feel really strongly about obviously things like accuracy and ethical standards in my daily life when I talk to other human beings, whether it's as a reporter or not. What I think is really interesting about technologies, whether it's

GBT or something else is the way in which we can sort of play with these ideas of how people are supposed to communicate in ways that are, I think, pretty interesting and freeing. After you got some feedback on the first couple of chapters, you asked the chatbot if it's okay to share a couple of more chapters. And chat GBT answered, absolutely, feel free to share more chapters. I'm looking forward to reading them and continuing our discussion. And that gets to a very fundamental question that you asked ChatGBTBT about, which is when a chatbot uses the first person, I, what exactly does it mean because it is not a person? It is not an I. It is artificial intelligence. It's a computer program. It's basically a machine. So what is the

eye? What does that mean that chatbot's using I? Yeah, I mean, I would argue that that I is a fictional creation of the company OpenAI that created ChatGBTBT. So we think about these technologies, I think, sometimes as being very separate from human experience and human desires and goals. But in fact, there's this company called Open AI whose investors want it to be very financially successful. And the way to be financially successful is to get a lot of people using a product. The way to get a lot of people using a product is to make people feel comfortable with the product, to trust the product. And one device that a company might use in order to do that is to have the product use language that makes you feel a bit like you're talking to another

person. So in reading chat GPT's responses to your chapters, one of the biases you noticed was that it suggested you add more about the positive side of AI and its creators. I thought that was interesting. Did that say to you that it was revealing the chatbot's bias or pointing out your negative bias or both? It's such an interesting question and it gets to the heart, I think, of what is problematic about these technologies because I can't claim to have any way of knowing why it said what it did. So basically, I fed at these chapters about big technology companies and I said, what feedback do you have for me? And it said, you could be more positive.

And then later it goes on to provide these sample paragraphs that thinks I should include in the book about how Sam Altman, the CEO of OpenAI, is a visionary leader who's also a pragmatist, like this really glowing stuff. It would be fun to be able, and it would support a strong critique to be able to say, oh, clearly Open AI has built this product in such a way that it's deletionable. liberately having the products about this propaganda about its CEO that's positive. It's certainly possible that that's the case, but there are all kinds of other explanations for it, too. It's possible that the language that the technology behind the chatbot absorbed in order to learn, quote, unquote, how to produce language happens to be somewhat biased toward people like Sam Altman.

There are all kinds of possible reasons, and we just don't know. But I think that not knowing is a problem. Did you use any of the chatbot's advice about balancing your reactions to AI and including more positive aspects of it? I didn't. So one thing that I wanted to be really thoughtful about was actually not writing a book that was influenced in any way by the rhetoric of the chatbot that I was then conversing with about the book. And so I wrote the entire book. And after doing that, I fed it to the chatbot. And certainly later, there were these edits that I made in the editing process with my editors at my publishing company. But those were not in response to integrating anything that the chatbot said, because on a philosophical level, I did not want to integrate anything the chatbot suggested. So you asked the chatbot about how it seemed programmed to flatter and to sound empathetic. kind, because before it gives you any kind of criticism ever, it tells you, like, this is very

well written, and this brings out, like, a combination of, like, tech history with your personal history. And, oh, I have to say, let me just interject here, that just to see what happened, I asked Chowchee P.T, what questions would Terry Gross ask Wahini Vara in a fresh air interview. And it was very flattering to me. It praised me as a good interviewer with like sensitivity and deep questions. So, you know, just another example that it can be very flattering. So you ask it about how it seemed programmed to flatter and to sound empathetic and kind. And it responded, the way I communicate is designed to foster trust and confidence in my responses, which can be both helpful and potentially misleading. And I thought, that's so true.

It can be helpful and misleading. And I thought maybe the chatbot is actually very transparent. So OpenAI has said that ChatGBTGBT and his other products are designed to foster trust, to appear helpful. So it says those things explicitly. And right, by saying this is how I function, yeah, I guess ChatGBTBT is being as transparent as it can be. I don't know that I would trust it to always be as transparent as that or even to know how to be transparent, right? Because it's just a machine that's generating words. It has no way of definitively always generating material that's even accurate, right? And so I have fairly low confidence that that transparency is always going to be there. I am curious, though, about what you thought of the questions that it produced, whether any of them were like at all interesting to you. They were kind of pretty broad, general questions. They all touched on themes in your book.

Yeah. They were all subjects I wanted to explore, but they were so, like, broad in nature that, you know, there was no, there was no personality. I'm not saying, like, well, look at my personality, but there was no point of view, and there was no follow-up. It was just like a list of questions, but there was no follow-up to try to go deeper after the answer. And I know it wouldn't have heard your answer, but still, when I prepare an interview, like one question leads to the next question to go deeper into that answer. And there was nothing like that. Yeah. Well, what's interesting, I think, about that.

And what I experienced, too, using ChatGPT in the context that I did is that there's something fundamental about human communication, like two people talking to each other or the fact that right now, for example, you and I are talking to each other, but I imagine you always also have an awareness of the fact that eventually millions of other people will hear the same conversation. And so both you and I are keeping in mind like this kind of complex idea about who we're communicating to, what the communication is for, and like our own backgrounds and experiences and ways of communication. communicating come into it. And a chatbot is like not doing any of that. It seems like it is because the words it produces sound kind of like the language humans use. But it's not using language in any way that's remotely like how we do. We're listening to Terry's interview with tech reporter and fiction writer Wahini Vara. Her new book is called Searches, Selfhood in the Digital Age. We'll hear more of their conversation after a short break. I'm Sam Brigger and this is Fresh Air Weekend.

So based on your interactions with AI, what are your thoughts about chat box and the use of AI for writing or editing? It wasn't that useful for you. It was very instructive about AI. But do you think there are other people that it would be very useful for? There was a study out of Cornell a couple of years ago that I found really interesting where they had some people write an essay about social media, just on their own. And then they gave these two other groups special AI models. For one group, they gave them an AI model that was predisposed to produce positive opinions about social media. And then they gave this other group an AI model that was predisposed to produce negative opinions about social media.

What they found was that when people wrote essays with the help, quote unquote, of these AI models, they were twice as likely to produce essays that reflected. the quote-unquote opinion of the AI model, it seems from that research and other research that's emerged since then that even if we are using these AI companies products to edit our work or ask for feedback on our work, there's a real danger that the responses that we're going to get are going to change our writing in fundamental ways

that we might not even be aware of. Your father uses AI, including to write haiku. So how does he use it and what do you think of that? Oh, my gosh, we could do a whole interview about my dad's use of AI. My dad has recently started sending me messages on WhatsApp where the whole text of the message is something he asked ChatGBTBT to write. So, for example, he recently sent me one that was, it's hard to decide whether to retire in Canada, the United States or India. here are some pros and cons for each option. So he never said to me, I'm wondering whether I should move to India or Canada for my retirement.

He just sent me that response. And so the subtext, like what he's communicating through chat GPT, is the thing that's actually unsaid. And so there are a lot of people out there. I think my dad is one of many people who want to communicate something. My dad was explaining to me on the phone the other day that he's not a writer. He can't communicate these things himself. But if he gives ChatGBT, GBT, enough of a prompt, it can communicate the thing he wants it to communicate. And there are things that I find problematic about that, for sure.

You know, AI in some ways is being used like a personal Cyrano de Bergerac. Like, you want to express your love for someone. You don't have the words. So you have this other guy write it as if you're saying it and signing your name to it. Yeah. So how do you use AI for real in your life? So the truth is that I use AI in very limited ways. The fact that I fed large portions of this book to chat DBT might give people the impression that I'm some huge AI super user, which I'm not. I'm a journalist who writes about AI. So to the extent that that's part of my work, I think it's really important for me to engage with the products. at the same time, I'm really concerned about all the things we don't know about how these products function and how the companies behind these products might ultimately use everything we're putting into their

products to exploit us, to expand their own wealth and power. I sometimes use ChatGBTGBT. A use that comes to mind is like if there's a word on the tip of my tongue, I'll go to ChatGBTGBT and write a sentence and with a blank in it and kind of explain the gist of what I'm looking for. And one thing it's pretty good at is coming up with what that word was that was on the tip of my tongue. So that's a small example of how I use it. When I do use it, I tend not to log into it. I tend to just go to chat GPT, use the interface without logging in so that my use of it is not associated with my account. I do still have an account because, again, as a journalist, I want to be able to access to these products. So I'm unclear since I've only used it twice each time to ask good

questions to help me understand how it worked for the interview was about to do, as I did in your case, because, you know, AI is at the center of the interview, so I wanted to ask it some meta questions. Yeah. But, you know, I used it for free. I don't have an account. I just put my question in, and it came up with stuff. What are some of the ways you expect it to be monetized in the future that it's not monetized for yet? Because I feel like being able to use it at all for free is kind of like a teaser until like no one can use it for free.

I'm just speculating. I have no knowledge. Yeah. So I'm speculating to an extent to. But these products are really, really expensive to build. And so investors are putting a lot of money. Companies themselves are putting a lot of money into building these products. and some small number, some small percentage of users are paying for premium versions of the product,

but that's just not enough to turn these companies into the enormous businesses that the investors are betting that they are going to be. And so that leaves us in this really interesting situation in 2025 where the companies are starting to say, okay, we're going to need to figure out how to monetize our free users, is how they put it. And the CFO of OpenAI said to the Financial Times last year that the company is looking into advertising as an option. Other AI companies, and here I'm talking about big companies like Google and Microsoft also seem to be thinking about this. So this is speculation, but here's one way in which it would be obvious for AI companies to monetize our use of the products. when people trust these products a lot, they end up going to these products with all kinds of personal information, their marital struggles, their conflict with their boss at work. And while we focus a lot on the question of like how accurate or unbiased or useful the information is that these products are giving us, I think something we kind of forget about is everything we're providing to the makers of these products in,

asking them these questions about really intimate details of our lives. And so eventually these companies are going to know a lot about who we are, about what kind of language can be used with each specific user to persuade them of something, to influence them in a particular way. And that puts these companies in a position to, for example, recommend products to us using language that's geared toward us specifically and our circumstances and our vulnerabilities and ultimately collect this huge database of all of us who are using these products, who we are and what makes us tick. Yeah, and it sounds like, you know, as you're saying that AI and the companies that own the AI products are going to know a lot more than, say, knowledge based on what

I searched for on Google or the books I bought on Amazon or the TV shows I'm watching on Netflix or the algorithms are going to recommend what I want to buy or watch next. Exactly. Yeah. Is the Internet and social media making you feel obsolete as a novelist? And also worried that all your writing, your essays, your journalism will be appropriated by AI. Yeah. I mean, what I would like to think is that we have choices here. And part of the reason that in this book and when I think about my own personal use of these products, I'm so interested in like our choice and agency in the matter is that if it's the case that big technology companies are just going to continue to amass more wealth and power and AI is here. And so AI is going to be even bigger in the way. the future and take everything over, like, that suggests that we don't have a choice in the

matter, right? However, if we say we have a choice in the matter and we can actually decide to choose a different future because we are unhappy with the one we're currently in, then we can potentially build a future that's different from the one that we're in now. But I think like in 2025, we're in this really interesting crucial period where not as many people are using AI as I think we think. So in the U.S., for example, most people have never tried chat GPT still in 2025. And so we're in this interesting position where we can actually decide as individuals, as communities, as societies, the extent to which we want AI to be a part of the future. the extent to which we want AI generating novels or generating something that is going to substitute a newspaper or magazine article or a radio show.

Thank you. It was really great to talk with you. I really enjoyed it. And thank you again for coming in spite of the fact that your windshield shattered on the way over. I should let you go and get it repaired before it rains or whatever. I appreciate it. This was so fun. It was a real honor to get to talk to you, Terry. Wahini Varra's new book is called Searches, Selfhood in the Digital Age. She spoke with Terry Gross. Singer-songwriter Billy Joel is a subject of a new two-part five-hour documentary on HBO. It's called Billy Joel, and so it goes, and looks at his life and career to date in a way that our TV critic, David B. and Cooley, says as both insightful and unflinching. Here's his review. When I was young, I worked on an oyster boat. I used to look up at this mansion on the hill and wonder what would it be like to live in a house like that.

I used to think, they're rich bastards. They never had to work a day in their life. Well, I own that house now. It's not finished yet, then neither am I. The full title of HBO's new Billy Joel documentary reveals a lot about the approach that co-directors Susan Lacey and Jessica Levin, who also collaborated on Jane Fonda in Five Acts, are taking.

The program is called Billy Joel and So It Goes. And the subtitle refers to one of the singer-songwriter's most introspective and intricate compositions. Structurally, and Structurally, and So, It Goes. so it goes, taps into Joel's lifelong love of classical music. It's a challenging piece, intentionally sprinkled with dissonant notes and unresolved chords. Joel sees his life that way. That's why I wrote it, he says, of the song. And Lacey and Levin present their artistic biography of Billy Joel the same way. A lot of attention is paid to process, what inspired certain songs, and how they were written and recorded. But the dissonant

of Joel's personal life is not shied away from. Multiple marriages and divorces, repeated visits to rehab centers for alcoholism, serious conflicts with managers and fellow musicians. It's all included. Not just from Joel's point of view either. We hear from his sister and stepbrother, his now-grown daughter, his ex-wives, his former bandmates and managers, and even from a series of rock critics whose career assessment of Joel's musical output often was less than kind. And we also hear from such musical peers as Paul McCartney, Garth Brooks, and Sting. All of those interviews are anything but perfunctory, and certainly aren't presented just to make Joel look better in retrospect.

How he met and eventually married his first wife, Elizabeth, is a story dramatic enough for a daytime soap opera. She provides her account of their relationship in honest, direct, in ultimately fawn terms, and so does he. His second wife, supermodel Christy Brinkley, is similarly candid, so much so that at several points she fights back tears. Joel, though, tells his own story with a certain emotional distance, acknowledging his own mistakes, but also noting and often forgiving the mistakes of others.

His biggest unresolved issue has to do with his own father, a classical musician who abandoned the family early, leaving Billy and his sister to be raised by a single mom. But before he left, Billy's father did notice young Billy's creative approach to piano lessons. One thing I remember, I was supposed to be playing the Moonlight Sonata. Must have been about eight years old. And rock and roll was around at that point.

And I started playing, instead of playing... I started playing... He came down the stairs, bam! I got whacked. And I got waxed so hard. He knocked me out. I was unconscious for like a minute. And I remember waking, I'm going,

going, well, that got his attention. Susan Lacey, whose other credits include running the outstanding PBS Arts Biography Series American Masters, knows a good story when she sees one, and as producer, knows how to tell it. Some parts of the narrative are built around his biggest hits. For example, a dispute with his first manager led Billy Joel to book himself into a piano bar under an assumed name, Bill Martin, because Martin was Billy's middle name. That experience led directly to the early breakout hit Piano Man, a song that became so familiar that in his later concert days,

he could stop singing it at any point and the audience would take over. We learn the inspirations for New York State of Mind, Just the Way You Are, Vienna, Baby Grand, and others. The billboard sales of songs and albums is charted, but so is the often lukewarm or dismissive critical response. We see him fighting back from near bankruptcy after being swindled by his manager and establishing long-running concert runs with Elton John and as a solo act at Madison Square Garden.

We're shown his creative bursts and his destructive behaviors and watch as he retires from writing lyrics, then performing, before he's lured back to appear at a benefit concert after Hurricane Sandy, which devastated his beloved community of Long Island. The reception to that 2012 appearance led Billy Joel on a new path and more than a decade of concert appearances followed. So did such awards as the Gershwin Prize for Songwriting and the Kennedy Center honors and the record-setting Madison Square Garden residency that ran off and on for 10 years.

The documentary ends with Joel performing Piano Man at one of those concerts, but that footage is interspersed with film from 1970s. of Joel at the piano singing the same song the day he signed his recording contract at Columbia Records. As Joel says in this documentary of his life to date, it is not a finished story. But as told in Billy Joel and so it goes, it is a very revealing one. David B. Incouli is professor of television studies at Rowan University. He reviewed the new HBO documentary called Billy Joel, and So It Goes. Coming up, we hear from Michael Grinbaum, author of the new book, Empire of the Elite.

Inside Condonast, the Media Dynasty that reshaped America. I'm Sam Brigger, and this is Fresh Air Weekend. For decades, one company in Manhattan, told the world what to buy, what to value, what to wear, what to eat, even what to think. That's how my guest Michael Grinbaum opens his new book about Condé Nass publications. Grinbaum writes that, quote, Vogue chose the designers whose clothes would be worn by millions around the world and the models who became global icons of sex and femininity.

Vanity Fair determined which moguls we envied and movie stars we worshipped. GQ made it okay for straight guys to care about clothes. Architectural Digest, pioneered real estate porn, and the New Yorker elevated tabloid fare like the O.J. Simpson murder trial to the realm of serious journalism. At the peak of its powers, Condé Nass cultivated a mystique that captivated tens of millions of subscribers across four continents with brands that became international symbols of class and glamour, unquote.

Grimbaum describes Condes. Nass today as a husk of its former self, in part because of how financial problems have reshaped tastes and how social media allows influencers to set trends and celebrities to post their own news and photos. Grinbaum's new book is called Empire of the Elite, Inside Kandai Nass, the media dynasty that reshaped America. He's a correspondent for the New York Times covering the intersection of media, politics, and culture. Michael Grinbaum, welcome to fresh air. What is the larger significance of Anna Wintour giving up her role as American Vogue's editorial director after 37 years, but keeping her title as global editorial director and chief content officer for Condé Nass? So she's still overseeing Wired Vanity Fair, GQ, Vogue, and several more magazines, but not the New Yorker.

She is stepping down from the role of editor-in-chief of Vogue magazine, which she has held since 1988. and it is a sign that the company is now starting to think about succession. But it actually surprised me and it stunned many inside Condé Nast. I spoke to Vogue staffers who were blindsided. They got called into a 9 a.m. meeting and Anna Wintour said that she was making this seismic change in her title. And it speaks to this major transitional moment that Condé Nast and really glossy magazines are enduring right now writ large. people no longer read print magazines the way they used to. And Vogue, it still is a global brand. It still has recognition around the world. But, you know, now there are thousands of influencers and social media channels where people get ideas about dressing and glamour and clothing and taste. And this is kind of the central conflict that I wanted to explore in this book was, Condé Nass was, I argue, one of the great cultural institutions of 20th century America. I actually compare it to the great Hollywood studios of the 30s, a culture factory that manufactured a vision of luxury and good taste and beamed it out to the rest of the country.

And what I was curious about was how such a powerful group of cultural tastemakers could so miss the changes in our culture and end up in this attenuated state that they're in today. You define the kind of style and status that define Kandai Nas publications at its peak in the 80s and 90s as, money luxury and celebrity so but you know money luxury and celebrity means different things to different people so what kind of money luxury and celebrity are we talking about yeah well i mean kane nest was always its magazines were always aimed i i put in the book as the upper classes and those that aspired to join them um and and actually i don't want to skip ahead but the company's history kind of goes back to the gilded age which is when their first was an American leisure class when there was a new group of Americans who were socially mobile,

upwardly mobile, who had disposable income for the first time, and were looking to find ways to express themselves through clothing, through interior decorating. So the company has a long history of appealing to this kind of upper middle brow audience. In the 1980s, this was the Gordon Gecko Wall Street era, and the magazines, especially Vanity Fair, which Tina Brown edited from 1983 to 1992, that really captured this flaunt of the era, a time when people were celebrating materialism, were celebrating consumption. One of the most interesting historical facts I stumbled on in my research was that the first issue of Tina Brown's Vanity Fair hit newsstands when the first episode of Lifestyles and the Rich and Famous debuted on American

broadcast television. And I think that tells you everything you need to know. And she's somebody who intentionally tried to combine high and low culture. And by low culture, I think you mean pop culture, street fashion. So talk a little bit about that combination and why it was something new. Tina Brown called this the mix. And actually, the high high-low blend is so absorbed into our media today that it's almost hard to believe it didn't exist back then. If you think about on our phones, on an average day, on Instagram or TikTok, you will swipe through, you know, a long policy discussion about the Trump administration's latest move, and then you'll swipe to some feature about the Kardashians, and then you'll go to a

swimsuit ad, and then you'll read something about menswear, and then you'll go back to something about what's happening in India or Australia, that kind of, I almost call it a manic media landscape that we exist in today. Back in the early 80s, when there were only so many magazines and newspapers that we consumed, most of them were very specifically focused. And so you might get Time magazine to find out what happened in the news that week. You might read the Atlantic Monthly for something more literary. What Tina Brown did, she created this blend where you would have a smart political profile about Gary Hart, who was trying to be the vice presidential candidate in 1984, and then a beautiful Annie Leibovitz photograph spread of, say, Daryl Hannah, and then a short story by, you know, Norman Mailer or Gore Vidal. And this was really unlike anything that was in the market back then. you know, readers hadn't really experienced something like this.

So having money and showing that you had money was very important to sign Newhouse, the owner of Condi Nast in the era that we're talking about, the 80s, the 90s. And he wanted his editors to not only help set fashion trends, but to and help choose which celebrities were important. He wanted his editors to be celebrities and to reflect the same kind. of luxury that the people they were writing about had. And to help them do that, he kind of subsidized some of them to be able to afford things that would look like they were really wealthy. I call them influencers before influencers. The idea was that the editor-in-chief,

their entire life should be a top-to-bottom marketing campaign for their magazine and for Condé Nast, the company. So I'll give you a few examples. If you were editor-in-law, chief of a Condoness magazine. You had a full-time black town car on demand, usually with a driver that would take you out to any event you needed to go, wait for you on the sidewalk, pick you up, bring you home. You would fly first class to Europe or anywhere you need to go for travel. A lot of people had wardrobe allowances if you were at the fashion magazines. I talked to editors who would come in with a $40,000 annual clothing allowance, and that was considered modest by Condonet's standards back then.

Clothing for themselves? Yes, to wear out at events, you know, to meet with advertisers, to be out at fashion shows, to essentially wear the flag of Condé Nass, to project this idea that we were the best of the best, and you better listen to what we have to say. And Syneuhaus didn't skimp when it came to expenses in the magazine either. Like, they actually rented an elephant and moved it into an office for a photo. So I won't tell the whole story, but you get the point of how extravagant that must be to just cleaning up after the elephant would have cost a lot of money. You'd think that they would get a stock image.

You know, you could easily – this was in 2008, so you could easily get a stock image off the Internet of an elephant. But at Condi Nest, you had to do things right. So they spent $30,000 to rent an elephant, which they trucked from Connecticut down to Brooklyn for the photo shoot. and this all happened two weeks before Lehman Brothers went bankrupt. Right. And this was about the kind of financial instruments that helped bankrupt financial institutions and caused the whole financial meltdown. And the article was about the elephant in the room, thus the elephant.

So these expenses took their toll on Condi Nast. In 1988, Fortune magazine uncovered that Conte Nast really wasn't making much money. You want to talk about what they were really making? Yeah. So all of the spending to outsiders seemed irrational and made no sense. How could you be splashing out so much for fashion shoots and, you know, editors and writers to have these luxurious lives? There was an internal logic to it, which is that Condoness was all kind of predicated on a myth. And the entire organization for many years, it was built around propagating this idea that they were,

untouchable, that there was a mystique to everyone in this charm company. And that's what made readers want to subscribe to own a piece of that fantasy land. And it made the advertisers from luxury brands want to buy pages in these magazines because they felt that they could make their products part of the fantasy. So there was a business model behind it. And I don't want to suggest that Sign Newhouse was overly wasteful. He didn't love to lose money. But what Fortune Magazine discovered in 1998 is that compared to their rivals and there's a Hearst, Time Life, some of the other big magazine empires, Condé Nass, their profits were so razor thin.

I mean, they were just barely in the black. And this is back when magazines were a hugely lucrative and profitable business. Condé Nass, they just spent, they spent on photo shoots. They felt that waste was an important part of creativity. That was one of the guiding maxims within the company. And what Fortune Magazine discovered is that, you know, it actually wasn't making a whole lot of money in the first place. I mean, it really wasn't as rich and wealthy as they made it out to be. So I kind of date that as one of the first moments where there were some dense in the armor, so to speak, of what Condé Nast had.

You could make the argument, and you do make it in the book, that Cy Newhouse, the owner of Condé Nast, helped turn Donald Trump into a national celebrity. He was profiled in GQ by Graydon Carter, who later became the editor of Vanity Fair. And also he owned the company that published the art of the deal. Let's start with the profile. What was the profile by Graydon Carter in GQ like and what was the cover photo like?

And remind us of what year this was, too. So in May 1984, GQ arrives on New York. who stands. There's a Richard Avedon portrait of this handsome 38-year-old businessman. He's in a suit. He has bushy eyebrows. He has kind of an ambiguous smile. And there's a big headline on the page, success, how sweet it is. The man in the photograph is Donald Trump. The profile inside is this portrait of a New York-Araveist, this up-and-coming real estate developer who wears flashy cufflinks, drives around in a burgundy limousine with DJT Vanity Plates. And it's an incredible story.

You know, Graydon Carter, who eventually had this years-long rivalry with Donald Trump because he used to make fun of him so much in his magazines, actually was one of the originators of this myth of Donald Trump because this was one of the first major national magazine articles that featured him. Was the tone snarky or admiring? Well, it was dry. I'd say that. I would say that Graden made clear that he was skeptical of this up-and-comer. He quotes him in the limousine, sort of driving past Trump Tower, admiring his own handiwork in this self-regarding way. So I think the basic DNA of this individual is present, even when we go back and read this story from 40 years ago. And you think that it's likely that Cy Newhouse knew

Donald Trump through Roy Cohn. When Cy Newhouse was in high school at the Horace Mann School for Boys, he and Roy Cohn went to the same school that were very close friends. Roy Cohn legally represented, Syne Newhouse and the company in some instances. And of course, Roy Cohn had been Donald Trump's mentor after Roy Cohn was a legal, you know, a legal aid to Senator Joseph McCarthy during the witch hunt, the communist witch hunting era. And another thing Roy Cohn is famous for, in the 1950s when it was against federal policy

to allow gay people to work in the federal government, Roy Cohn helped to expose people who were in the closet. And of course, he's famous from the fictionalized version of him in Angels in America. He's one of the most notorious figures in 20th century America. And one of the most notorious closeted gay figures. That as well. And what very few people know is that he was Cy Newhouse's best friend for his entire life.

They carpooled to school together when they were young teenagers. And when Roy Cohn was on trial for corruption charges, Cy Newhouse sat in the courthouse day after day as a show of support. This was long after Roy Cohn had been disgraced. So it's very likely that Cy had met Trump at one of Cohn's part. parties. And what happens in 1984 is that Sai, who kept very close track, by the way, of the sales of his magazines, he would sit there with a rubber finger actually going through the accounting numbers every month in his office. He saw that this GQ issue sold like gangbusters. For whatever reason, the readers, young men, presumably, were responding to Donald Trump. And so he had bought Random House, which was the prestigious New York publisher. And Cy knew went to his executives and he said, this guy should write a book. And in fact, I spoke to the editor of Art of the Deal who told me that it was uniquely Cy Newhouse's idea that Trump

create Art of the Deal. And describe what he did to try to sell Trump on the idea of having a book. So Trump was a little skeptical and he agreed to take a meeting in his Trump Tower office. So So Synew House actually went in person. What they did was they brought a mockup of a hardcover book. It was kind of a big hefty. I think it was a Russian novel, actually, that they put kind of a like a fake dust jacket on. A fake Trump dust jacket. It had a big photograph of Trump on it in the Trump Tower atrium. And Trump kind of stares at it for a moment and he pauses. And then he says, please make my name much bigger. And then he agreed. So I paid him $500,000, which I don't have the math on hand, but I mean, this was back in 1984. And when the book came out, there was a huge

book party with all of New York society under the waterfall in Trump Tower, where many years later he would come down the escalator. And there's some amazing photos of Cy Newhouse standing right there next to him. And this was the book that really catapulted Trump away from just being, you know, a tabloid curiosity and sort of an interest of New York City, but really into a national phenomenon. And it was on the bestseller list for just about two years. It earned millions for the company. It was a huge pop cultural phenomenon at the time. What's so interesting is, now, Sanyahuas died in 2017. I wasn't able to interview him for the book, but I did speak with his daughter.

And I raised the subject of Art of the Deal and Cy's unseen hand in Trump's legacy. And she cringed when I brought it up with her. It was clearly a painful topic. She told me, I just don't know whether Trump would have gotten that show. the apprentice, but for the success of the book. So my father, in a way, put Donald Trump on the map. It's a source of deep regret to everybody to think that, but how would he have ever known? Michael Grinbaum, it's really been great to talk with you. Thank you so much. Thank you for having me. It's been a pleasure. Michael Grinbaum is the author of the new book, Empire of the Elite,

inside Condy Nast, the media dynasty that reshaped America. Fresh Air Weekend is produced by Teresa Madden. Fresh Air's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. For Terry Gross and Tanya Mosley, I'm Sam Brigger. Support for NPR and the following message come from the Walton Family Foundation, working to create access to opportunity for people and communities by tackling tough social and environmental problems. More information is at walton family foundation.org.

Thank you.